Dichloromethane → 8-Chloro-4-[3-(2-hydroxymethyl-6-methyl-pyridin-4-yl)-phenyl]-7-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 498856Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12](C)[C:11](Cl)=[CH:10][C:9]=1[NH:16][C:17](=[O:42])[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[C:31]([CH2:33][O:34]C3CCCCO3)[N:30]=[C:29]([CH3:41])[CH:28]=2)[CH:22]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[CH2:51]([Cl:53])Cl>>[Cl:53][C:51]1[C:12]([CH3:11])=[CH:13][C:8]2[N:7]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[CH:28]=[C:29]([CH3:41])[N:30]=[C:31]([CH2:33][OH:34])[CH:32]=4)[CH:22]=3)[CH2:18][C:17](=[O:42])[NH:16][C:9]=2[CH:10]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 86589465HCID 86589465, compound

Product 1

HCID 223172528-Chloro-4-[3-(2-hydroxymethyl-6-methyl-pyridin-4-yl)-phenyl]-7-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from (RS)-[4-chloro-5-methyl-2-(3-{3-[2-methyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-4-yl]-phenyl}-3-oxo-propionylamino)-phenyl]-carbamic acid tert-butyl ester (Example M297) (0.45 g, 0.74 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a light brown solid (200 mg, 67%).

Sources & evidence

ORD record: ord-a98cf76e43de4155bdbbddb4e8162aff
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949542B2

Reaction notes

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